(Methanol-κO)(2-methyl-3-nitro­benzoato-κO)triphenyl­tin(IV)

Yip, F.W.; Teoh, S.G.; Yamin, B.M.; Ng, S.W.

doi:10.1107/S1600536810033623

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page m1164

https://doi.org/10.1107/S1600536810033623

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(Methanol-κO)(2-methyl-3-nitrobenzoato-κO)triphenyltin(IV)

Foo Win Yip,^a Siang Guan Teoh,^b Bohari M. Yamin ^c and Seik Weng Ng ^d ^*

^aDepartment of Chemical Science, Faculty of Science, Universiti Tunku Abdul Rahman, 31900 Kampar, Malaysia, ^bSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 Penang, Malaysia, ^cSchool of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangbaan Malaysia, 43600 Bangi, Malaysia, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 19 August 2010; accepted 20 August 2010; online 28 August 2010)

The five-coordinate Sn atom in the title compound, [Sn(C₆H₅)₃(C₈H₆NO₄)(CH₃OH)], exists in a trans-C₃SnO₂ trigonal-bipyramidal coordination polyhedron of which the O atoms of the methanol molecule and carboxylate group occupy the apical sites. In the crystal, adjacent molecules are linked by intermolecular O—H⋯O interactions, generating a helical hydrogen-bonded chain running along the b axis.

Related literature

For other methanol/ethanol-coordinated triphenyltin carboxylates, see: Alcock & Roe (1989 ); Gao et al. (2006 ); Lo & Ng (2009 ); Ma et al. (2004 ); Ng (1998 , 1999 ); Wang et al. (2007 ); Yeap & Teoh (2003 ); Yin et al. (2002 ).

Experimental

Crystal data

[Sn(C₆H₅)₃(C₈H₆NO₄)(CH₄O)]
M_r = 562.17
Monoclinic, P 2₁ /n
a = 10.8385 (13) Å
b = 14.8791 (18) Å
c = 15.8243 (19) Å
β = 94.004 (2)°
V = 2545.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.04 mm⁻¹
T = 293 K
0.40 × 0.25 × 0.10 mm

Data collection

Bruker SMART diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.681, T_max = 0.903
15231 measured reflections
5739 independent reflections
4515 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.115
S = 1.08
5739 reflections
313 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.15 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn1—C1	2.118 (4)
Sn1—C7	2.110 (4)
Sn1—C13	2.121 (4)
Sn1—O1	2.146 (2)
Sn1—O5	2.410 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O2ⁱ	0.85 (1)	1.87 (2)	2.676 (4)	158 (5)
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810033623/bt5330sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810033623/bt5330Isup2.hkl

checkCIF report

Comment top

Triphenyltin(IV) carboxylates generally exist as tetrahedral molecules in which the carboxylate anion is only unidentate to the tin atom. However, there are examples of such compounds having an alcohol molecule into its coordination sphere, as noted in several examples (Alcock & Roe, 1989, Gao et al., 2006; Lo & Ng, 2009; Ma et al., 2004; Ng, 1998; Ng, 1999; Wang et al., 2007; Yeap & Teoh, 2003; Yin et al. 2002). The alcohol (either methanol or ethanol) serves as the reaction medium. The condensation of triphenyltin hydroxide and 2-methyl-3-nitrobenzoic acid in methanol gave the expected product as a methanol-coordinated compound (Scheme I, Fig. 1). The five-coordinate tin atom in Sn(C₆H₅)₃(CH₄O)(C₈H₆NO₄) exists in a trans-C₃SnO₂ trigonal bipyramidal coordination polyhedron for which the O atoms of the methanol and carboxylate occupy the apical sites. As found in the other examples, the tin-oxygen_alcohol bond is longer than the tin-oxygen_carboxylate bond (Table 1). However, the C₃Sn girdle is nearly planar [Σ_angles 358.6 (5) °]. Adjacent molecules are linked by an O–H···O interaction to generate a helical hydrogen-bonded chain running along the b-axis of the monoclinic unit cell (Fig. 2, Table 2).

Related literature top

For other methanol/ethanol-coordinated triphenyltin carboxylates, see: Alcock & Roe (1989); Gao et al. (2006); Lo & Ng (2009); Ma et al. (2004); Ng (1998, 1999); Wang et al. (2007); Yeap & Teoh (2003); Yin et al. (2002).

Experimental top

Triphenyltin hydroxide (0.73 g, 2 mmol) and 2-methyl-3-nitrobenzoic acid (0.36 g, 2 mmole) were heated in methanol (50 ml) for an hour. The mixture was filtered to give a clear yellow solution. The filtrate was set aside for the formation of crystals, which were isolated in 80% yield; m.p. 394.5 K. CHN&Sn elemental analysis for C₂₇H₂₅N₁O₅Sn: C 57.53, H 4.04, N 2.45, Sn 21.02%. Calc.: C 57.68, H 4.48, N 2.49, Sn 21.11%.

Structure description top

For other methanol/ethanol-coordinated triphenyltin carboxylates, see: Alcock & Roe (1989); Gao et al. (2006); Lo & Ng (2009); Ma et al. (2004); Ng (1998, 1999); Wang et al. (2007); Yeap & Teoh (2003); Yin et al. (2002).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the title compound at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Hydrogen-bonded chain structure.

(Methanol-κO)(2-methyl-3-nitrobenzoato-κO)triphenyltin(IV) top

Crystal data top

[Sn(C₆H₅)₃(C₈H₆NO₄)(CH₄O)]	F(000) = 1136
M_r = 562.17	D_x = 1.467 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 918 reflections
a = 10.8385 (13) Å	θ = 2.7–25.1°
b = 14.8791 (18) Å	µ = 1.04 mm⁻¹
c = 15.8243 (19) Å	T = 293 K
β = 94.004 (2)°	Block, yellow
V = 2545.7 (5) Å³	0.40 × 0.25 × 0.10 mm
Z = 4

Data collection top

Bruker SMART diffractometer	5739 independent reflections
Radiation source: fine-focus sealed tube	4515 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→13
T_min = 0.681, T_max = 0.903	k = −18→19
15231 measured reflections	l = −20→10

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0581P)² + 1.4418P] where P = (F_o² + 2F_c²)/3
5739 reflections	(Δ/σ)_max = 0.001
313 parameters	Δρ_max = 1.15 e Å⁻³
1 restraint	Δρ_min = −0.29 e Å⁻³

Crystal data top

[Sn(C₆H₅)₃(C₈H₆NO₄)(CH₄O)]	V = 2545.7 (5) Å³
M_r = 562.17	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.8385 (13) Å	µ = 1.04 mm⁻¹
b = 14.8791 (18) Å	T = 293 K
c = 15.8243 (19) Å	0.40 × 0.25 × 0.10 mm
β = 94.004 (2)°

Data collection top

Bruker SMART diffractometer	5739 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4515 reflections with I > 2σ(I)
T_min = 0.681, T_max = 0.903	R_int = 0.024
15231 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	1 restraint
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 1.15 e Å⁻³
5739 reflections	Δρ_min = −0.29 e Å⁻³
313 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Sn1	0.63268 (2)	0.197738 (16)	0.687848 (16)	0.04465 (10)
O1	0.6379 (3)	0.32447 (16)	0.62345 (18)	0.0566 (7)
O2	0.7358 (3)	0.40787 (19)	0.72344 (18)	0.0635 (7)
O3	0.7290 (6)	0.5035 (5)	0.3367 (3)	0.140 (2)
O4	0.7949 (6)	0.6315 (4)	0.3673 (4)	0.160 (2)
O5	0.6168 (3)	0.05094 (19)	0.7505 (2)	0.0617 (7)
H5	0.679 (3)	0.016 (3)	0.758 (3)	0.089 (17)*
N1	0.7459 (5)	0.5650 (4)	0.3876 (4)	0.0993 (15)
C1	0.8227 (4)	0.1658 (3)	0.6847 (3)	0.0530 (9)
C2	0.8560 (5)	0.0862 (3)	0.6479 (3)	0.0705 (12)
H2	0.7951	0.0485	0.6236	0.085*
C3	0.9784 (7)	0.0619 (5)	0.6469 (4)	0.103 (2)
H3	0.9998	0.0074	0.6231	0.124*
C4	1.0676 (6)	0.1176 (7)	0.6805 (5)	0.118 (3)
H4	1.1502	0.1008	0.6801	0.141*
C5	1.0378 (5)	0.1978 (5)	0.7148 (5)	0.108 (2)
H5A	1.1001	0.2360	0.7368	0.130*
C6	0.9150 (4)	0.2230 (3)	0.7172 (3)	0.0756 (14)
H6	0.8946	0.2780	0.7405	0.091*
C7	0.5464 (4)	0.2443 (3)	0.7950 (2)	0.0512 (9)
C8	0.5951 (5)	0.2284 (4)	0.8764 (3)	0.0766 (13)
H8	0.6674	0.1951	0.8851	0.092*
C9	0.5383 (7)	0.2609 (5)	0.9442 (4)	0.0999 (19)
H9	0.5728	0.2496	0.9986	0.120*
C10	0.4323 (7)	0.3094 (4)	0.9338 (4)	0.101 (2)
H10	0.3944	0.3312	0.9806	0.121*
C11	0.3822 (6)	0.3257 (4)	0.8546 (5)	0.1000 (19)
H11	0.3093	0.3585	0.8471	0.120*
C12	0.4384 (5)	0.2940 (3)	0.7847 (4)	0.0764 (14)
H12	0.4035	0.3061	0.7306	0.092*
C13	0.5186 (3)	0.1510 (2)	0.5826 (2)	0.0473 (8)
C14	0.3968 (4)	0.1301 (3)	0.5878 (3)	0.0704 (12)
H14	0.3631	0.1296	0.6402	0.085*
C15	0.3226 (5)	0.1094 (4)	0.5146 (4)	0.0900 (17)
H15	0.2396	0.0954	0.5187	0.108*
C16	0.3702 (6)	0.1096 (3)	0.4381 (4)	0.0908 (18)
H16	0.3198	0.0972	0.3895	0.109*
C17	0.4918 (7)	0.1280 (4)	0.4322 (3)	0.0914 (17)
H17	0.5257	0.1258	0.3799	0.110*
C18	0.5658 (5)	0.1501 (3)	0.5044 (3)	0.0701 (12)
H18	0.6486	0.1644	0.4997	0.084*
C19	0.6831 (4)	0.3978 (3)	0.6536 (3)	0.0520 (9)
C20	0.6661 (4)	0.4765 (2)	0.5946 (2)	0.0493 (9)
C21	0.5921 (4)	0.5464 (3)	0.6191 (3)	0.0634 (11)
H21	0.5564	0.5429	0.6708	0.076*
C22	0.5704 (5)	0.6205 (3)	0.5691 (4)	0.0773 (15)
H22	0.5198	0.6666	0.5861	0.093*
C23	0.6240 (5)	0.6255 (3)	0.4942 (4)	0.0747 (14)
H23	0.6111	0.6757	0.4597	0.090*
C24	0.6958 (4)	0.5577 (3)	0.4699 (3)	0.0660 (11)
C25	0.7200 (4)	0.4793 (3)	0.5179 (3)	0.0589 (10)
C26	0.8001 (6)	0.4023 (4)	0.4908 (4)	0.0979 (18)
H26	0.8447	0.3771	0.5397	0.147*
H26B	0.8576	0.4242	0.4522	0.147*
H26C	0.7486	0.3569	0.4634	0.147*
C27	0.5104 (5)	0.0158 (4)	0.7849 (4)	0.0936 (18)
H27A	0.5287	0.0021	0.8437	0.140*
H27B	0.4849	−0.0380	0.7550	0.140*
H27C	0.4450	0.0594	0.7794	0.140*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.04851 (16)	0.03856 (15)	0.04577 (16)	0.00015 (10)	−0.00464 (10)	0.00265 (10)
O1	0.0819 (19)	0.0289 (12)	0.0569 (16)	−0.0078 (12)	−0.0114 (14)	0.0025 (11)
O2	0.087 (2)	0.0475 (15)	0.0527 (16)	−0.0111 (14)	−0.0160 (15)	0.0024 (13)
O3	0.152 (5)	0.195 (6)	0.075 (3)	−0.012 (4)	0.021 (3)	−0.002 (4)
O4	0.187 (5)	0.158 (5)	0.139 (5)	−0.054 (4)	0.028 (4)	0.063 (4)
O5	0.0636 (18)	0.0493 (15)	0.073 (2)	0.0051 (13)	0.0088 (15)	0.0157 (14)
N1	0.099 (3)	0.111 (4)	0.087 (4)	−0.007 (3)	0.003 (3)	0.037 (3)
C1	0.050 (2)	0.054 (2)	0.055 (2)	0.0003 (17)	0.0007 (17)	0.0189 (19)
C2	0.078 (3)	0.069 (3)	0.066 (3)	0.012 (2)	0.018 (2)	0.012 (2)
C3	0.098 (5)	0.114 (5)	0.103 (5)	0.041 (4)	0.040 (4)	0.027 (4)
C4	0.061 (4)	0.165 (8)	0.130 (6)	0.031 (4)	0.031 (4)	0.067 (6)
C5	0.054 (3)	0.130 (6)	0.140 (6)	−0.019 (3)	−0.005 (3)	0.047 (5)
C6	0.063 (3)	0.069 (3)	0.093 (4)	−0.010 (2)	−0.011 (3)	0.024 (3)
C7	0.056 (2)	0.045 (2)	0.052 (2)	−0.0054 (16)	0.0022 (17)	−0.0023 (17)
C8	0.075 (3)	0.100 (4)	0.053 (3)	−0.004 (3)	−0.007 (2)	−0.002 (3)
C9	0.108 (5)	0.135 (6)	0.056 (3)	−0.030 (4)	0.007 (3)	−0.015 (3)
C10	0.115 (5)	0.104 (5)	0.090 (5)	−0.041 (4)	0.048 (4)	−0.040 (4)
C11	0.085 (4)	0.091 (4)	0.128 (6)	0.008 (3)	0.033 (4)	−0.020 (4)
C12	0.078 (3)	0.077 (3)	0.074 (3)	0.015 (2)	0.006 (3)	−0.005 (2)
C13	0.058 (2)	0.0339 (17)	0.049 (2)	0.0034 (15)	−0.0081 (17)	−0.0018 (15)
C14	0.067 (3)	0.077 (3)	0.066 (3)	−0.015 (2)	−0.010 (2)	−0.003 (2)
C15	0.077 (3)	0.094 (4)	0.095 (4)	−0.026 (3)	−0.024 (3)	−0.001 (3)
C16	0.127 (5)	0.061 (3)	0.077 (4)	−0.014 (3)	−0.044 (4)	−0.006 (3)
C17	0.124 (5)	0.096 (4)	0.052 (3)	0.005 (4)	−0.011 (3)	−0.015 (3)
C18	0.076 (3)	0.076 (3)	0.058 (3)	0.008 (2)	−0.003 (2)	−0.013 (2)
C19	0.059 (2)	0.045 (2)	0.052 (2)	0.0048 (17)	−0.0002 (19)	−0.0010 (17)
C20	0.061 (2)	0.0312 (16)	0.054 (2)	−0.0017 (15)	−0.0105 (18)	−0.0013 (15)
C21	0.072 (3)	0.042 (2)	0.074 (3)	0.0043 (18)	−0.010 (2)	−0.0046 (19)
C22	0.085 (3)	0.042 (2)	0.101 (4)	0.015 (2)	−0.020 (3)	0.002 (2)
C23	0.078 (3)	0.044 (2)	0.097 (4)	0.001 (2)	−0.031 (3)	0.014 (2)
C24	0.071 (3)	0.067 (3)	0.059 (3)	−0.008 (2)	−0.007 (2)	0.015 (2)
C25	0.069 (3)	0.044 (2)	0.062 (3)	0.0004 (18)	0.001 (2)	0.0051 (18)
C26	0.122 (5)	0.088 (4)	0.088 (4)	0.030 (3)	0.039 (4)	0.010 (3)
C27	0.095 (4)	0.065 (3)	0.124 (5)	0.001 (3)	0.034 (4)	0.022 (3)

Geometric parameters (Å, º) top

Sn1—C1	2.118 (4)	C11—C12	1.383 (8)
Sn1—C7	2.110 (4)	C11—H11	0.9300
Sn1—C13	2.121 (4)	C12—H12	0.9300
Sn1—O1	2.146 (2)	C13—C18	1.371 (6)
Sn1—O5	2.410 (3)	C13—C14	1.364 (6)
O1—C19	1.275 (5)	C14—C15	1.397 (7)
O2—C19	1.218 (4)	C14—H14	0.9300
O3—N1	1.225 (7)	C15—C16	1.349 (8)
O4—N1	1.179 (6)	C15—H15	0.9300
O5—C27	1.410 (6)	C16—C17	1.356 (9)
O5—H5	0.850 (10)	C16—H16	0.9300
N1—C24	1.450 (7)	C17—C18	1.389 (7)
C1—C6	1.384 (6)	C17—H17	0.9300
C1—C2	1.378 (6)	C18—H18	0.9300
C2—C3	1.376 (8)	C19—C20	1.500 (5)
C2—H2	0.9300	C20—C21	1.385 (5)
C3—C4	1.354 (10)	C20—C25	1.384 (6)
C3—H3	0.9300	C21—C22	1.367 (6)
C4—C5	1.360 (10)	C21—H21	0.9300
C4—H4	0.9300	C22—C23	1.358 (8)
C5—C6	1.386 (8)	C22—H22	0.9300
C5—H5A	0.9300	C23—C24	1.346 (7)
C6—H6	0.9300	C23—H23	0.9300
C7—C8	1.378 (6)	C24—C25	1.407 (6)
C7—C12	1.383 (6)	C25—C26	1.517 (6)
C8—C9	1.363 (8)	C26—H26	0.9600
C8—H8	0.9300	C26—H26B	0.9600
C9—C10	1.357 (9)	C26—H26C	0.9600
C9—H9	0.9300	C27—H27A	0.9600
C10—C11	1.351 (10)	C27—H27B	0.9600
C10—H10	0.9300	C27—H27C	0.9600

C7—Sn1—C1	125.41 (16)	C11—C12—H12	119.8
C7—Sn1—C13	118.16 (15)	C18—C13—C14	118.4 (4)
C1—Sn1—C13	114.98 (16)	C18—C13—Sn1	118.6 (3)
C7—Sn1—O1	96.93 (13)	C14—C13—Sn1	122.7 (3)
C1—Sn1—O1	97.32 (13)	C13—C14—C15	120.2 (5)
C13—Sn1—O1	87.06 (12)	C13—C14—H14	119.9
C7—Sn1—O5	85.35 (13)	C15—C14—H14	119.9
C1—Sn1—O5	84.49 (13)	C16—C15—C14	120.6 (5)
C13—Sn1—O5	88.38 (12)	C16—C15—H15	119.7
O1—Sn1—O5	175.43 (10)	C14—C15—H15	119.7
C19—O1—Sn1	126.7 (3)	C17—C16—C15	119.7 (5)
C27—O5—Sn1	125.3 (3)	C17—C16—H16	120.1
C27—O5—H5	112 (4)	C15—C16—H16	120.1
Sn1—O5—H5	122 (4)	C16—C17—C18	120.0 (6)
O4—N1—O3	119.9 (7)	C16—C17—H17	120.0
O4—N1—C24	120.7 (7)	C18—C17—H17	120.0
O3—N1—C24	119.2 (5)	C13—C18—C17	120.9 (5)
C6—C1—C2	118.8 (4)	C13—C18—H18	119.5
C6—C1—Sn1	122.1 (4)	C17—C18—H18	119.5
C2—C1—Sn1	119.1 (3)	O2—C19—O1	126.0 (4)
C1—C2—C3	120.8 (6)	O2—C19—C20	119.9 (3)
C1—C2—H2	119.6	O1—C19—C20	114.1 (3)
C3—C2—H2	119.6	C21—C20—C25	120.7 (4)
C4—C3—C2	119.8 (6)	C21—C20—C19	117.4 (4)
C4—C3—H3	120.1	C25—C20—C19	121.8 (3)
C2—C3—H3	120.1	C22—C21—C20	121.5 (5)
C5—C4—C3	120.7 (6)	C22—C21—H21	119.2
C5—C4—H4	119.6	C20—C21—H21	119.2
C3—C4—H4	119.6	C21—C22—C23	118.8 (5)
C4—C5—C6	120.3 (6)	C21—C22—H22	120.6
C4—C5—H5A	119.9	C23—C22—H22	120.6
C6—C5—H5A	119.9	C24—C23—C22	120.0 (4)
C1—C6—C5	119.6 (6)	C24—C23—H23	120.0
C1—C6—H6	120.2	C22—C23—H23	120.0
C5—C6—H6	120.2	C23—C24—C25	123.8 (5)
C8—C7—C12	117.8 (4)	C23—C24—N1	117.5 (5)
C8—C7—Sn1	122.1 (3)	C25—C24—N1	118.6 (5)
C12—C7—Sn1	120.0 (3)	C20—C25—C24	115.1 (4)
C9—C8—C7	120.7 (5)	C20—C25—C26	120.7 (4)
C9—C8—H8	119.6	C24—C25—C26	124.2 (4)
C7—C8—H8	119.6	C25—C26—H26	109.5
C8—C9—C10	121.2 (6)	C25—C26—H26B	109.5
C8—C9—H9	119.4	H26—C26—H26B	109.5
C10—C9—H9	119.4	C25—C26—H26C	109.5
C11—C10—C9	119.3 (6)	H26—C26—H26C	109.5
C11—C10—H10	120.3	H26B—C26—H26C	109.5
C9—C10—H10	120.3	O5—C27—H27A	109.5
C10—C11—C12	120.6 (6)	O5—C27—H27B	109.5
C10—C11—H11	119.7	H27A—C27—H27B	109.5
C12—C11—H11	119.7	O5—C27—H27C	109.5
C7—C12—C11	120.3 (6)	H27A—C27—H27C	109.5
C7—C12—H12	119.8	H27B—C27—H27C	109.5

C7—Sn1—O1—C19	53.5 (3)	C1—Sn1—C13—C18	−35.2 (4)
C1—Sn1—O1—C19	−73.7 (3)	O1—Sn1—C13—C18	61.5 (3)
C13—Sn1—O1—C19	171.5 (3)	O5—Sn1—C13—C18	−118.4 (3)
C7—Sn1—O5—C27	46.3 (4)	C7—Sn1—C13—C14	−15.7 (4)
C1—Sn1—O5—C27	172.6 (4)	C1—Sn1—C13—C14	151.3 (3)
C13—Sn1—O5—C27	−72.1 (4)	O1—Sn1—C13—C14	−112.0 (3)
C7—Sn1—C1—C6	−48.3 (4)	O5—Sn1—C13—C14	68.2 (3)
C13—Sn1—C1—C6	145.8 (3)	C18—C13—C14—C15	−0.7 (7)
O1—Sn1—C1—C6	55.7 (4)	Sn1—C13—C14—C15	172.7 (4)
O5—Sn1—C1—C6	−128.6 (4)	C13—C14—C15—C16	0.1 (8)
C7—Sn1—C1—C2	132.7 (3)	C14—C15—C16—C17	1.6 (9)
C13—Sn1—C1—C2	−33.2 (4)	C15—C16—C17—C18	−2.6 (9)
O1—Sn1—C1—C2	−123.4 (3)	C14—C13—C18—C17	−0.3 (7)
O5—Sn1—C1—C2	52.4 (3)	Sn1—C13—C18—C17	−174.1 (4)
C6—C1—C2—C3	2.9 (7)	C16—C17—C18—C13	2.0 (8)
Sn1—C1—C2—C3	−178.1 (4)	Sn1—O1—C19—O2	3.2 (6)
C1—C2—C3—C4	−1.5 (9)	Sn1—O1—C19—C20	−176.5 (3)
C2—C3—C4—C5	−0.5 (10)	O2—C19—C20—C21	−64.5 (5)
C3—C4—C5—C6	1.2 (11)	O1—C19—C20—C21	115.2 (4)
C2—C1—C6—C5	−2.2 (7)	O2—C19—C20—C25	116.6 (5)
Sn1—C1—C6—C5	178.8 (4)	O1—C19—C20—C25	−63.7 (5)
C4—C5—C6—C1	0.2 (9)	C25—C20—C21—C22	−0.5 (6)
C1—Sn1—C7—C8	−23.2 (4)	C19—C20—C21—C22	−179.4 (4)
C13—Sn1—C7—C8	142.3 (4)	C20—C21—C22—C23	−0.7 (7)
O1—Sn1—C7—C8	−127.3 (4)	C21—C22—C23—C24	0.8 (7)
O5—Sn1—C7—C8	56.6 (4)	C22—C23—C24—C25	0.2 (7)
C1—Sn1—C7—C12	155.6 (3)	C22—C23—C24—N1	177.2 (5)
C13—Sn1—C7—C12	−38.8 (4)	O4—N1—C24—C23	48.4 (8)
O1—Sn1—C7—C12	51.5 (4)	O3—N1—C24—C23	−126.4 (6)
O5—Sn1—C7—C12	−124.5 (4)	O4—N1—C24—C25	−134.5 (6)
C12—C7—C8—C9	−0.1 (7)	O3—N1—C24—C25	50.7 (8)
Sn1—C7—C8—C9	178.8 (4)	C21—C20—C25—C24	1.4 (6)
C7—C8—C9—C10	0.3 (9)	C19—C20—C25—C24	−179.7 (4)
C8—C9—C10—C11	0.0 (10)	C21—C20—C25—C26	−179.5 (5)
C9—C10—C11—C12	−0.4 (10)	C19—C20—C25—C26	−0.6 (6)
C8—C7—C12—C11	−0.3 (7)	C23—C24—C25—C20	−1.3 (7)
Sn1—C7—C12—C11	−179.2 (4)	N1—C24—C25—C20	−178.3 (4)
C10—C11—C12—C7	0.6 (9)	C23—C24—C25—C26	179.6 (5)
C7—Sn1—C13—C18	157.8 (3)	N1—C24—C25—C26	2.6 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O2ⁱ	0.85 (1)	1.87 (2)	2.676 (4)	158 (5)

Symmetry code: (i) −x+3/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₃(C₈H₆NO₄)(CH₄O)]
M_r	562.17
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.8385 (13), 14.8791 (18), 15.8243 (19)
β (°)	94.004 (2)
V (Å³)	2545.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.04
Crystal size (mm)	0.40 × 0.25 × 0.10

Data collection
Diffractometer	Bruker SMART
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.681, 0.903
No. of measured, independent and observed [I > 2σ(I)] reflections	15231, 5739, 4515
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.115, 1.08
No. of reflections	5739
No. of parameters	313
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.15, −0.29

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Sn1—C1	2.118 (4)	Sn1—O1	2.146 (2)
Sn1—C7	2.110 (4)	Sn1—O5	2.410 (3)
Sn1—C13	2.121 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O2ⁱ	0.85 (1)	1.87 (2)	2.676 (4)	158 (5)

Symmetry code: (i) −x+3/2, y−1/2, −z+3/2.

Acknowledgements

We thank Universiti Tunku Abdul Rahman (Vote No. 6200/Y02) and the University of Malaya for supporting this study.

References

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